Phosphoesters are abundant in carbohydrate structures, yet their chemical reactivity is less well known than that of nucleoside
phosphoesters. Both classes of compounds contain sugar bound phosphoesters, but structural versatility of carbohydrates means that the
reactivity range is wider, and reaction mechanisms not feasible in nucleic acid chemistry, are possible. Sugar phosphates, as well as their
phosphodiester and phosphoanhydride derivatives with a phosphate group in glycosylic position, react like acetals under acidic conditions.
Substrates with a phosphate group attached to an alcoholic OH react by intramolecular transesterification similar to that of RNA
provided that there is a suitably positioned HO-group and a suitable leaving group. If there is a free carbonyl group allowing anomeric
equilibria, base-catalyzed phosphate elimination through enediolate intermediates may compete with the cleavage, particularly under alkaline
conditions. The few reports on phosphate migration show that the reaction is conceivable, but the competition between cleavage
and phosphate migration possibly is different from reactions of nucleic acids and nucleotides.
Keywords: Biological phosphate, Carbohydrate, Hydrolysis, Phosphate migration, Phosphodiester bond, Sugar phosphate, Sugar nucleotide.
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